[Remote] Director, Marketing AI Transformation

Note: The job is a remote job and is open to candidates in USA. Toast creates technology to help restaurants and local businesses succeed in a digital world. They are seeking a transformation leader to drive AI adoption and workflow redesign across their Marketing organization, focusing on integrating AI into daily work and fostering a culture that embraces this change.ResponsibilitiesDefine and implement a comprehensive AI transformation roadmap aligned with marketing leadership's strategic direction and overall business objectivesTranslate strategic bets into sequenced adoption plans that account for team readiness, tool maturity, and infrastructure dependenciesIdentify and prioritize the workflows where AI creates the most leverage and build the playbook for redesigning themBuild and run programs that drive sustained AI adoption, including practical enablement resources, scalable training programs, and change management approaches that meet teams where they areOwn the metrics that distinguish real adoption from performative adoption, tracking workflow changes and behavior shifts rather than training completion rates aloneChampion a culture where marketers see AI as a tool for creativity and efficiency rather than a disruption to manageDesign and implement the standards, review processes, and decision frameworks that let teams move fast while maintaining brand consistency, quality, and complianceEstablish how AI generated content gets reviewed before it ships, how parallel agent builds get evaluated and consolidated, and how we define quality when AI is generating at volumeNavigate the tension between speed and standardization, building systems that enable bothPartner with marketing leaders to break roles down into workflows and identify which should be automated, redesigned, or augmented with AIBuild transition plans that move teams from current state to AI augmented operationsServe as the bridge between what gets built by the GTM engineering team and what gets adopted by marketing teamsRecruit, onboard, and support 1 to 2 Champions per marketing team who serve as local AI resources and early adoptersGive Champions a platform (dedicated Slack channels, demo slots, direct line to the GTM engineering team) and use them as a feedback loop for what is working and what is notScale peer to peer knowledge sharing as the primary mechanism for broad adoptionBuild the measurement framework for AI transformation: adoption rates, workflow efficiency gains, time savings, and output qualityDesign executive facing dashboards that give leadership honest, clear visibility into where AI is delivering value and where it is notPartner with HR to factor AI proficiency into performance expectationsPartner with the GTM Engineering team to receive validated use cases and ensure smooth handoff from build to adoptionCoordinate with R&D/BTT on foundational data dependenciesPartner with Sales Operations on Sales-led GTM AI initiatives to ensure we are alignedSkills8+ years in marketing operations, marketing strategy, or marketing transformation, with experience leading change management or organizational transformation programs at scaleDemonstrated experience embedding emerging technology (AI or otherwise) into marketing workflows across a large organization (200+ person marketing team preferred)Deep understanding of how marketing teams actually work: campaign operations, content production, demand generation, brand, analytics. You know where AI creates genuine leverage versus where it creates noiseTrack record of building programs that drive measurable, sustained behavior change, not just awareness or training completion rates, but actual workflow adoptionExperience designing governance frameworks for new capabilities at scaleStrong communication and presentation skills with the ability to present transformation progress to senior leadership with clarity and honesty, including when things are not workingComfort with ambiguity. This is a role where the playbook is still being writtenExperience at a company that has gone through a similar AI transformation within marketingFamiliarity with the B2B SaaS marketing tech stack (MAPs, CRMs, ad platforms, data visualization platforms, etc.) and how AI tools connect to itExperience with AI specific tooling ecosystems: Claude/Anthropic, Gemini, agent frameworks, MCP integrationsBenefitsCash compensation (overtime, bonus/commissions if eligible)EquityBenefitsHybrid work model that fosters in-person collaboration while valuing individual needsReasonable accommodations for persons with disabilities to enable them to access the hiring processCompany OverviewToast is a point-of-sale and restaurant management platform designed for businesses in the food service and hospitality industry. It was founded in 2011, and is headquartered in Boston, Massachusetts, USA, with a workforce of 1001-5000 employees. Its website is https://pos.toasttab.com.Company H1B SponsorshipToast has a track record of offering H1B sponsorships, with 3 in 2026, 26 in 2025, 32 in 2024, 39 in 2023, 66 in 2022, 29 in 2021, 17 in 2020. Please note that this does not guarantee sponsorship for this specific role.